Flawless Sabrina was born in the late 1950's as the alter-ego to south Philly fag, and trained psychologist, Jack Doroshow. Informed by the insights of leading transsexualism expert Harry Benjamin, Sabrina is a tongue in cheek reaction to absurd society. Flawless Sabrina began her career in the 1950's and 60's as a radical business woman and renegade, operating a national drag beauty pageant aptly named The Nationals. Her counter-cultural beauty queen enterprise spanned a decade, and ended by the making of an iconic documentary called The Queen that debuted in 1968.

Flawless' career in show business continued in the late 60's and onto the 70's when she worked as a consultant on films like Midnight Cowboy, Butch Cassidy and the Sundance Kid, and Myra Breckinridge. In Hollywood her assumed expertise of homosexual matters was meant to inform the film industry at a time when queer subject matter was tentatively addressed in cinema.

In later years Sabrina became involved in politics, having worked with Hilary Clinton to enable transgender people to alter the (M/F) sex marker on their U.S. passport, and for gay marriage. She is an active member of her community, and a go-to resource for trans in the arts and politics. In late 2013 Sabrina worked closely with luxury department store Barneys on their groundbreaking transgender themed ad campaign shot by Bruce Weber.

Flawless Sabrina's lifetime encouragement of queer community is a subversive reaction to American society. To her countless children, the artists and queers who she admires, Sabrina reiterates the importance of an individual's empowerment, always encouraging people to follow their heart, sit in the driver's seat, and allow life's mysteries to unveil naturally.